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Hypericin

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Identification
Molecular formula
C30H16O8
CAS number
548-04-9
IUPAC name
10-hydroxy-8-(10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3,4-dihydrobenzo[g]isochromen-8-yl)-7-methoxy-3-methyl-3,4-dihydrobenzo[g]isochromene-1,6,9-trione
State
State
Hypericin is a solid at room temperature.
Melting point (Celsius)
320.00
Melting point (Kelvin)
593.15
Boiling point (Celsius)
625.00
Boiling point (Kelvin)
898.15
General information
Molecular weight
504.44g/mol
Molar mass
504.4420g/mol
Density
1.6400g/cm3
Appearence

Hypericin typically appears as a reddish-brown powder. It is known for its strong coloration and fluorescence properties under ultraviolet light. In its natural state, it is found in St. John's wort (Hypericum perforatum) and is often extracted from this plant.

Comment on solubility

Solubility of 10-hydroxy-8-(10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3,4-dihydrobenzo[g]isochromen-8-yl)-7-methoxy-3-methyl-3,4-dihydrobenzo[g]isochromene-1,6,9-trione

The solubility of this complex compound presents some intriguing characteristics that are worth discussing. Primarily, the solubility can be influenced by several factors, including polarity and intermolecular interactions. Here are some key points:

  • Polarity: Given that the compound has multiple functional groups, such as hydroxyl (–OH) and methoxy (–OCH3), these can increase its polar characteristics, enhancing its solubility in polar solvents like water and alcohols.
  • Hydrogen Bonding: The presence of hydroxyl groups suggests that the compound can engage in hydrogen bonding with other molecules. This interaction typically leads to increased solubility in solvents capable of similar bonding.
  • Influence of Molecular Structure: The molecular framework—consisting of fused aromatic rings—might decrease solubility in certain solvents due to potential stacking interactions that could stabilize the solid phase compared to its dissolved state.
  • Solvent Compatibility: While the compound may exhibit varying solubility in polar and non-polar solvents, it may dissolve better in organic solvents such as dimethyl sulfoxide (DMSO) or ethanol, as opposed to non-polar solvents due to its polar functional groups.
  • Temperature Dependency: The solubility is likely to vary with temperature, where an increase in temperature generally leads to higher solubility for most solid compounds.

In conclusion, while the solubility of this compound is complex and possibly limited in aqueous environments, its solubility characteristics exhibit various dependencies that could be critical for its application and use in different fields. Understanding these nuances can provide significant insights into its chemical behavior in practical scenarios.

Interesting facts

Exploring 10-hydroxy-8-(10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3,4-dihydrobenzo[g]isochromen-8-yl)-7-methoxy-3-methyl-3,4-dihydrobenzo[g]isochromene-1,6,9-trione

This complex compound, often referred to as a potent derivative of natural products, exemplifies the fascinating world of organic chemistry and the intricate design of molecular structures.

Key Features

  • Bioactivity: This compound has attracted attention for its potential biological activities, including anti-inflammatory and antioxidant properties, which may imply utility in various therapeutic applications.
  • Structural Complexity: Its structure comprises multiple functional groups, including hydroxyl and methoxy groups, which are essential for its reactivity and biological interactions.
  • Natural Occurrence: Many compounds in this class are derived from plants and have been historically used in traditional medicine.

Chemical Significance

The unique arrangement of atoms in this compound gives it distinct properties that chemists study for advancing synthetic methodologies and understanding natural product chemistry. As a result, scientists are continually researching similar compounds to uncover new medicinal properties.

Applications

Research has indicated that compounds with similar structural motifs may hold promise in drug development. They can be studied for:

  • Developing new anti-cancer agents
  • Creating potential neuroprotective compounds
  • Exploring their role in enzymatic inhibition

In summary, 10-hydroxy-8-(10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3,4-dihydrobenzo[g]isochromen-8-yl)-7-methoxy-3-methyl-3,4-dihydrobenzo[g]isochromene-1,6,9-trione is not only a mouthful to say but also a treasure trove of possibilities for scientists eager to explore the bounds of organic chemistry and sustainable medicine. As one researcher aptly noted, "The simplicity of nature's design leads us to complex discoveries." This compound truly embodies that philosophy.

Synonyms
Xanthomegnin
1685-91-2
Xanthomegnine
10-hydroxy-8-(10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3,4-dihydrobenzo[g]isochromen-8-yl)-7-methoxy-3-methyl-3,4-dihydrobenzo[g]isochromene-1,6,9-trione
NSC264720
NSC-264720
DTXSID60937500
NS00126315
3,3'-bis(2-methoxy-5-hydroxy-7-(2-hydroxypropyl)-8- carboxyl-1,4-naphthoquinone lactone)
[8,2-c]pyran]-1,1',7,7',10,10'-hexone, 3,3',4,4'-tetrahydro-6,6'-dihydroxy-9,9'-dimethoxy-3,3'-dimethyl-, (3R,3'R)-
[8,2-c]pyran]-1,1',7,7',10,10'-hexone, 3,3',4,4'-tetrahydro-6,6'-dihydroxy-9,9'-dimethoxy-3,3'-dimethyl-, [R-(R*,R*)]-
[8,3-c]pyran]-1,1',6,6',9,9'-hexone, 3,3',4,4'-tetrahydro-10,10'-dihydroxy-7,7'-dimethoxy-3,3'-dimethyl-, [R-(R*,R*)]-
10,10'-Dihydroxy-7,7'-dimethoxy-3,3'-dimethyl-3,3',4,4'-tetrahydro-1H,1'H-[8,8'-binaphtho[2,3-c]pyran]-1,1',6,6',9,9'-hexone
10,10'-Dihydroxy-7,7'-dimethoxy-3,3'-dimethyl-3,3',4,4'-tetrahydro-1H,1'H-8,8'-bibenzo[g]isochromene-1,1',6,6',9,9'-hexone
10-hydroxy-8-{10-hydroxy-7-methoxy-3-methyl-1,6,9-trioxo-3H,4H-naphtho[2,3-c]pyran-8-yl}-7-methoxy-3-methyl-3H,4H-naphtho[2,3-c]pyran-1,6,9-trione